This is a common issue that many new and upcoming hosting companies will face. For the first few months you might be able to handle everything by yourself, but as your company grows it will become more apparent that you need to start offloading the workload to other people.

There is a point when either the workload of supporting your customers will either become too great to handle, issues will become more complicated, or you start to lose clients because you can't be on 24/7 and provide them with an adequate level of support necessary to keep them happy.

It is this point in the timeline that some companies never move on and expand, and they will always be the very definition of the 1 man host. For those that decided to jump over to the next step it will come in two variations, either you can hire a remote staff, or find an outsourced support company to handle it for you. There are a few benefits & negatives for both.

Hiring a freelancer
(Benefits)
€ Can find pretty much anybody willing to work under your budget.
€ They can feel like they are a part of your company, and put in a level of passion and devotion to help it grow.
€ Can hire locally, or remotely, in any city, state, or country.
(Negatives)

€ Can be a hit or miss as far as ability to provide adequate support or server management.
€ Works during your assigned shift hours, meaning they are unlikely going to be available in an emergency.
€ Lose motivation and provide poorer performance, show up late or not at all - no accountability.
€ Depending on who you hire there is a risk they could potentially damage or destroy your company, and since they are likely to be in a different part of the world, or country it would be too expensive to try and pursue legal action.

Hiring an Outsourced Support Company
(Benefits)
€ The company can find a tech unique to your company and your requirements for their job
€ Company will train/manage the technician and be accountable if the employee doesn't show up or is sick.
€ The company will likely provide some kind of 24/7 coverage allowing you to get emergency assistance or support even if it is outside of the service you are paying for
€ Overtime the team or technician will become familiar with your company/setup and be able to build upon his or her existing knowledge to help provide a better experience for your customers.
€ If the tech is performing poorly, there is always the manager or owner of the support company willing to step in and make things right.
(Negatives)

€ Less ability to negotiate over price, and the type of support provided will be dependent on your budget, such as whether you can afford shared techs, or a dedicated tech.
€ The techs will never be able to work with you locally if you ever decide to establish an office
€ The support will be limited to just that, support. They would not likely be able to switch to handle a billing or a sales position.

So there you have it, a few negatives & benefits for hiring a freelancer or going through a company. Without any personal bias, it is justifiably easier to go through an outsourced company because in the end they are managing the employee, and taking what would be another hat you'd have to wear (HR Department) when running your hosting company. Ultimately though I think it would be more beneficial to have a remote freelancer working for you to handle sales/billing issues and take phone calls as well. This would allow you to keep a closer eye on the issues more closely relating to the revenue your company generates.